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Enantioselective Synthesis of -Amino Acids
Second Edition
edited by
Eusebio Juaristi
and Vadim Soloshonok

Enantioselective Synthesis of -Amino Acids covers all facets of the synthesis of -amino acids.

Enantioselective Synthesis of -Amino Acids, Second Edition updates reviews included in the First Edition while also covering new developments since its publication.

Enantioselective Synthesis of -Amino Acids presents detailed discussions of the most important methods for the synthesis of -amino acids.

In most cases, the lead chemist who originally developed a method provides an authoritative description of it.

In addition, Enantioselective Synthesis of -Amino Acids, Second Edition:

  • Features introductory overviews on the structural types of relevant -amino acid targets and salient -amino acids present in natural products
  • Dedicates several chapters to advances in the synthesis of oligomers from -amino acids
  • Includes general and practical procedures for the preparation of -amino acids in each chapter
  • Discusses the most important methods that have been recently developed for the asymmetric synthesis of cyclic and open-chain -amino acids
  • Includes a report on the preparation of libraries of enantiopure -amino acids using combinatorial approaches
Enantioselective Synthesis of -Amino Acids offers upper-level students and professionals an essential resource for pharmaceutical development, medicinal chemistry, and biochemistry.

Contents:

  1. Structural Types of Relevant b-Amino Acid Targets
    • 2-Alkyl--Amino Acids
    • 3-Alkyl--Amino Acids
    • 2,2-Disubstituted -Amino Acids
    • 2,3-Disubstituted -Amino Acids
    • 3,3-Disubstituted -Amino Acids
    • 2,3,3-Trisubstituted -Amino Acids
    • 2,2,3,3-Tetrasubstituted -Amino Acids
    • 2-Aryl--Amino Acids
    • 3-Aryl--Amino Acids
    • Olefinic and Alkynyl--Amino Acids
    • α,-Diamino Acids
    • α-Hydroxy--Amino Acids
    • -Amino-?-Hydroxy Acids
    • Carbocyclic -Amino Acids
    • Heterocyclic -Amino Acids

  2. -Amino Acids in Natural Products
    • Natural Products Containing -Amino Acids Related to Proteinogenic α-Amino Acids
    • Natural Products Containing Unusual Aliphatic -Amino Acids
    • Natural Products Containing Aliphatic Hydroxy--Amino Acids
    • Natural Products Containing Aliphatic -Amino Acids with Oxo Groups
    • Natural Products Containing Amino--Amino Acids (Except -Lysine)
    • Alicyclic and Heterocyclic -Amino Acids
    • Natural Products Containing Unusual Aromatic -Amino Acid

  3. Preparation of Enantiopure -Amino Acids by Homologation of a-Amino Acids
    • ArndtEistert Homologation
    • Homologation of Amino Acids with Concomitant -Lactam Formation
    • Homologation of Amino Acids Using Cyano Hydrins

  4. Asymmetric Catalysis in Enantioselective Synthesis of -Amino Acids
    • Catalytic Asymmetric Conjugate Addition for Preparation of -Aliphatic--Amino Acids
    • Asymmetric Mannich Reactions Catalyzed by Thiourea Derivatives for Enantioselective Preparation of -Aryl--Amino Acids

  5. Enantioselective Synthesis of Conformationally Constrained -Amino Acids
    • Cycloalkane -Amino Acids
    • Alkyl-Substituted -Amino Acids
    • Other Methodologies

  6. Catalytic Enantioselective Mannich Reactions
    • Catalytic Enantioselective Mannich Reactions Using Chiral Lewis Acid Catalysts
    • Catalytic Asymmetric Mannich Reactions via Metal Enolates
    • Catalytic Asymmetric Reaction Using an Organocatalyst

  7. Enantioselective Synthesis of -Amino Acids via Stereoselective Hydrogenation of -Aminoacrylic Acid Derivatives
    • Recent Developments: Rhodium Complexes with Chiral Phosphorus Bidentate Ligands
    • Recent Developments: Rhodium Complexes with Chiral Phosphorus Monodentate Ligands
    • Recent Developments: Ruthenium Complexes with Chiral Phosphorus Bidentate Ligands

  8. Asymmetric Synthesis of -Amino Acids by Enolate Additions to tert-Butanesulfinyl Imines
    • Synthesis of N-tert-Butanesulfinyl Imines
    • Synthesis of N-Sulfinyl-Protected -Amino Acids
    • N-tert-Butanesulfinyl Protecting Group
    • Synthetic Utility

  9. Organocatalytic Approaches to Enantioenriched -Amino Acids
    • Mannich-Type Reactions Using Aldehydes and α-Ethyl Glyoxylate
    • Mannich-Type Reactions Using Aldehydes and Preformed Aldimines
    • Three-Component Mannich Reactions Using Aldehyde Donors
    • Proposed Mechanism for L-Proline-Catalyzed Mannich Reactions
    • Transformation of Product of L-Proline-Catalyzed Mannich Reaction into -Amino Acid and -Lactams
    • One-Pot Transformations via L-Proline-Catalyzed Mannich Reactions Using Aldehydes as Nucleophiles
    • Mannich Reactions Using α,α-Disubstituted Aldehydes or α-Imidoaldehyde for Preparation of Highly Functionalized -Amino Acid Derivatives
    • Other Organocatalytic Reactions for Preparation of Enantioenriched -Amino Acids

  10. Asymmetric Synthesis of Cyclic &Beat;-Amino Acids via Cycloaddition Reactions
    • General Strategies in Asymmetric Synthesis of Cyclic -Amino Acids
    • Cyclic -Amino Acids via Cycloaddition Reactions
    • Synthesis of cis- and trans-2-Aminocyclohexanecarboxylic Acid Derivatives via [4 + 2]-Cycloaddition Reactions
    • Synthesis of -Proline Derivatives via [3 + 2]-Cycloaddition Reactions
    • Synthesis of Constrained Six-Membered Ring α,α-Disubstituted -Amino Acid Derivatives via [4 + 2]-Cycloaddition Reactions

  11. Enantioselective Synthesis of Novel -Amino Acids
    • Acyclic Amino Acids
    • Cyclic and Conformationally Constrained -Amino Acids

  12. Asymmetric Synthesis of Phosphonic Analogs of -Amino Acids
    • Enantioselective CC Bond-Forming Reactions
    • Enantioselective CN Bond-Forming Reactions
    • Enantioselective CH Bond-Forming Reactions

  13. Asymmetric Synthesis of α-Substituted--Amino Phosphonates and Phosphinates and -Amino Sulfur Analogs
    • Synthesis of α-Alkyl--Amino Phosphorus Derivatives
    • Synthesis of -Amino-α-Hydroxy Phosphonic and Phosphinic Acid Derivatives
    • Synthesis of -Amino-α-Halogenated Phosphonates
    • Synthesis of α, -Diamino Phosphonates and Phosphinates
    • -Amino-α-Substituted Phosphorus Derivatives with Peptide Bond Formation: -Amino-α-Substituted Phosphonoand Phosphinopeptides
    • -Amino Sulfur Analogs

  14. Stereoselective Synthesis of Fluorine-Containing -Amino Acids
    • Acyclic Fluorinated α, -Disubstituted -Amino Acids
    • Cyclic Fluorinated α, -Disubstituted -Amino Acids
    • α-Fluoroalkyl -Amino Acids
    • -Fluoroalkyl -Amino Acids
    • -Substituted α, α-Difluoro--Amino Acids

  15. Enantioselective Synthesis of -Amino Acids via Conjugate Addition to α, -Unsaturated Carbonyl Compounds
    • Diastereoselective Additions to Chiral Michael Acceptors
    • Additions of Chiral Ammonia Equivalents to Michael Acceptors
    • Methods Based on Asymmetric Catalysis

  16. Preparation of Enantiopure -Amino Acids via Enantioselective Conjugate Addition
    • Conjugate Addition of Alkyl or Aromatic Amines
    • Addition of Hydroxylamine to Enoates
    • Conjugate Addition of Azide
    • Conjugate Addition of Carbon Nucleophiles

  17. Biocatalytic Entry to Enantiomerically Pure -Amino Acids
    • Biocatalytic Entry to Enantiomerically Pure -Amino Acids

  18. Stereoselective Synthesis of -Amino Acids via Radical Reactions
    • Synthesis of Acyclic -Amino Acids
    • Synthesis of Cyclic -Amino Acids
    • Synthesis of -Lactams

  19. Recent Advances in Synthesis of a-Hydroxy--amino Acids and Their Use in SAR Studies of Taxane Anticancer Agents
    • Synthesis of Enantiopure α-Hydroxy--amino Acid Components of Taxane Anticancer Agents by -Lactam Synthon Method
    • New C-13 α-Hydroxy--amino Acid Residues and Their Significance in Second-Generation Taxoids
    • Taxoids with Photoaffinity-Labeled α-Hydroxy--amino Acid Residues
    • Taxoids with Fluorine- and Isotope-Labeled α-Hydroxy--amino Acid Residues for NMR Studies

  20. Synthesis of -Amino Acids and Their Derivatives from b-Lactams: Update
    • -Lactam Ring Opening by Oxygen Nucleophiles: -Amino Esters and Related Products
    • -Lactam Ring Opening by Nitrogen Nucleophiles: -Amino Amides and b-Amino AcidDerived Peptides
    • -Lactam Ring Opening by Carbon Nucleophiles: -Amino Ketones and Related Products
    • Large-Ring Heterocycles from -Lactams

  21. Multiple-Component Condensation Methods for Preparation of Combinatorial Libraries of -Amino Carbonyl Derivatives
    • Mannich Reaction
    • Other Multiple-Component Reactions
    • Solid-Phase MCC Methods

  22. Using Constrained b-Amino Acid Residues to Control -Peptide Shape and Function
    • Introduction: -Peptides in the Foldamer Context
    • Monomer Synthesis
    • -Peptide Synthesis
    • Conformational Data
    • Biological Applications
    • New Frontiers for -Peptide Structure

  23. 2-Amino Acids with Proteinogenic Side Chains and Corresponding Peptides: Synthesis, Secondary Structure, and Biological Activity
    • Synthesis of 2-Amino Acids
    • Solution and Solid-Phase Synthesis of Peptides Containing 2-Amino Acids
    • Secondary Structures of Peptides Containing 2-Amino Acids
    • Biologically Active Peptides Containing Proteinogenic 2-Amino Acids
Index

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Enantioselective Synthesis of -Amino Acids
Second Edition
edited by Eusebio Juaristi and Vadim Soloshonok

2005 634 pages $211.95 + shipping
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